反応 #1738

反応方程式

carbon dioxide

hydrochloric acid

n-butyl-lithium

ammonium chloride

(2-adamantan-1-yl-4-bromo-phenoxy)-tert-butyl-dimethylsilane

→

3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid

溶媒

hexane

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONSubsequently, the reaction mixture was firstly poured into ice-cold
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄After washing once with water
4. 4
   乾燥drying over sodium sulfate
5. 5
   その他evaporation there
6. 6
   その他was obtained a white, crystalline mass which
7. 7
   その他was recrystallized from ethyl acetate

実験手順

9.3 g of (2-adamantan-1-yl-4-bromo-phenoxy)-tert-butyl-dimethylsilane were dissolved in 120 ml of absolute tetrahydrofuran and treated dropwise at -78° C. with 15.5 ml of a 1.6 molar solution of n-butyl-lithium in hexane. After stirring at -78° C. for 1.5 hours, a vigorous stream of carbon dioxide was introduced for one hour. Subsequently, the reaction mixture was firstly poured into ice-cold, saturated, aqueous ammonium chloride solution, acidified cautiously to pH 3 with cold 2N hydrochloric acid and extracted with ethyl acetate. After washing once with water, drying over sodium sulfate and evaporation there was obtained a white, crystalline mass which was recrystallized from ethyl acetate and gave 7 g of 3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoic acid, m.p. 250°-252° C.

出典